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Virgin Island Sailing

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⛵ Wondering what it is like to charter a yacht?
From luxury catamarans and motor yachts to superyachts, there are countless options to choose from. The right yacht depends on your destination, group size, travel style, and personal preferences.
No matter your travel style, there is a charter experience designed for you:
🛥️ Superyacht Charters Exceptional privacy, larger professional crews, Michelin-level dining, jacuzzis, jet skis, water slides, luxury tenders, and extraordinary personalized service. Depending on the yacht, your crew will include a captain, one or more chefs, stewardesses, deckhands, engineers, dive instructors, wellness specialists, yoga instructors, personal trainers, event coordinators, and more.
🌴 Crewed Yacht Charters Always including a professional captain and gourmet chef, with some yachts featuring a third or fourth crew member for an even higher level of service. Many also offer sea scooters, e-foils, paddleboards, towable tubes, and other water toys for guests of all ages.
👨‍✈️ Captain-Only Charters A professional captain guides your journey. Many yachts include paddleboards, snorkeling gear, and fishing equipment, while some captains may also provide light meals, craft cocktails, or share their local knowledge and favorite fishing spots.
⚓ Bareboat Charters Take the helm and sail at your own pace. Previous boating experience is required for many destinations. For those beginning their sailing journey, the Virgin Islands are often considered one of the most approachable places to start. Our concierge team can also help with provisioning recommendations and other pre-arrival planning.
🤝 Shared Yacht Charters Reserve a private cabin and enjoy a yacht charter experience without chartering the entire yacht. It is a wonderful way to meet fellow travelers who share a passion for the ocean, adventure, and exploration while enjoying gourmet meals, paddleboards, snorkeling gear, floats, and sometimes kayaks.

💬 Comment YACHT and we will send you a link to explore yachts, destinations, and charter options.

#superyachts #superyachtcharter #michelinstarchef #starshipyacht #megayachtcharter by @vi_sailing

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4 months ago

Comment DESTINATION and we’ll send you our guide to the best times of year to sail the world’s most incredible charter destinations. ⛵✨

Since 1987, Virgin Island Sailing® has helped more than 10,000 happy clients experience the world from the water. We specialize in luxury catamaran charters, helping travelers find the right yacht and destination for the way they want to explore.

Where will you go? 🗺️

🏝️ Island-hop through the British Virgin Islands, go Painkiller tasting starting at the legendary Soggy Dollar, and time your charter for dancing beneath the moon at a Full Moon Party in Trellis Bay.

🐷 Explore the secluded cays of The Bahamas, Bahama Mama in hand. Swim with the famous pigs of the Exumas, snorkel through impossibly clear water, then drop anchor beside a secluded sandbar where it might be just you, your favorite people, and miles of turquoise.

🏛️ Sail through Greece, where ancient history, island life, and cinematic scenery come together. Explore centuries-old seaside towns and venture ashore to discover spectacular Greek locations chosen to bring Christopher Nolan’s The Odyssey to the big screen, including Pylos, Methoni, and the breathtaking shores of Voidokilia.

🐚 Escape to Tahiti and French Polynesia, where lagoons glow in almost unbelievable shades of blue. Sail toward iconic Bora Bora, snorkel among tropical marine life, encounter stingrays and manta rays, picnic on a secluded motu, and bring home an authentic Tahitian pearl from the islands where these treasures are cultivated.

And these are only a few of the places waiting to be explored. ✨

Swipe through our charter destinations, and keep going to the final slide for the complete list. 🌎

💌 Comment DESTINATION below and we’ll send our guide to the best times to sail each destination straight to your DMs.

#vacationofalifetime #catamaransailing #vacationmodeon😎 #virginislandsailing #yachtcharterbroker taken in Tortola, BVI by @vi_sailing

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2 months ago

⚡️ Sailing just got easier.

Online booking for bareboat charters is now live at Virgin Island Sailing®!

Look for the ⚡️ while browsing on virginislandsailing.com. The lightning bolt identifies vessels that are ready to book online, with real-time availability at your fingertips.

See the ⚡️? You can secure the yacht model, dates, and layout you prefer online, without waiting. Online booking is available on sailing catamarans, power catamarans, and monohull sailboats across our worldwide destinations. 🌎

No lightning bolt? You can still request a quote or place a courtesy hold, and one of our Charter Experts will assist you with your booking.

Our Charter Experts are always here when you need us. Online booking simply gives you a faster, more convenient way to secure your bareboat charter when you’re ready.

Ready to book online? Comment “BOOKING” below and we’ll DM you the link to our step-by-step guide. 👇
Online booking for crewed yacht charters is coming soon 👀 Stay tuned!

#bvisailing #bareboatcharter #catamarancharter #sailingvacation #VirginIslandSailing by @vi_sailing

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a month ago

⛵ Sailing School Spotlight: TMM Yacht Charters (@vi_sailing)

📍 Booth Location: Dock I
🌐 Website: https://sailtmm.com/
📘 Facebook: @sailingvacations

Meet the team from TMM Yacht Charters! We caught up with them at the Annapolis Sailboat Show to learn about their personalized charter experiences, sailing instruction, and unforgettable adventures in the British Virgin Islands (BVI).

🌊 What makes TMM Yacht Charters special?
TMM is a small, personalized charter company with a fleet of just 30 well-maintained vessels. Based in Tortola’s Road Harbour, they offer a welcoming experience where guests get to know the entire team, creating lasting relationships that bring sailors back year after year.

⛵ What’s one thing people might not expect about sailing with you?
You can earn your ASA certification while exploring the Caribbean! TMM offers instructional skippers and ASA courses, including ASA 114 for catamaran sailing. Whether you’re looking to improve your skills or simply enjoy a skippered vacation, they have options for different experience levels.

📍 What makes the BVI a great place to sail?
Guests can cruise from island to island, discovering beautiful destinations throughout the British Virgin Islands. Charters typically last seven days or longer, with a five-night minimum. Guests can also book a sleep-aboard to settle in, unpack, and relax before setting sail the next morning.

🎟️ Any boat show specials this week?
Yes! TMM Yacht Charters is offering 10% OFF charters across their fleet, with select vessels available at 15% OFF!

⚓ How can someone get started?
Visit sailtmm.com or stop by Dock I at the Annapolis Sailboat Show to explore their charter options, ASA courses, and sailing vacations!

#AmericanSailing #TMMYachtCharters #AnnapolisSailboatShow #LearnToSail #SailingSchool #BritishVirginIslands #YachtCharter #SailingVacation taken in Annapolis Boat Show by @vi_sailing

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2 days ago

St. Barth: Where Fame Meets Discretion 🥂

A favorite retreat among Hollywood stars, world-class athletes, celebrated musicians, and international tastemakers, St. Barth has long mastered the art of understated luxury.
Here, familiar faces are simply part of the scenery. Privacy is respected, discretion is second nature, and even the most recognizable guests can enjoy the island’s exceptional dining and effortless elegance away from the spotlight.
And this season, there’s even more to discover.
✨ Langosteria debuts at Cheval Blanc on October 22, with a sweeping terrace overlooking Flamands Bay.
✨ Loulou, the celebrated Parisian hotspot with a presence in Courchevel, arrives at Fouquet’s Saint-Barth this November, taking over the former Shellona beachfront location. @loulourestaurants
✨ Zuma opens November 25, bringing its internationally acclaimed contemporary Japanese cuisine to the island. @zumasaintbarth
✨ Cream, the latest concept from the indie hospitality group behind Pablo St. Barth, is coming to Gustavia. @cream.saintbarth
✨ Kinugawa makes its anticipated return, this time in Saint-Jean. @kinugawaofficial
🍾 St. Barth Gourmet Festival returns November 9–15 for its 13th edition, bringing together distinguished chefs and culinary enthusiasts for a celebration of exceptional cuisine.
🩵 Enjoy performances by David Guetta, Black Coffee and/or Hugel at some of St. Barth’s most exclusive venues @gypsea_stbarth @lagueritebeach_saintbarth @nikkibeachsaintbarth

In a destination accustomed to extraordinary guests, the greatest luxury is simply being yourself.

Discover St. Barth With a Private Yacht Charter.

After the Virgin Islands, St. Barth is among our most requested charter destinations. At Virgin Island Sailing®, our Charter Experts know the island, its marinas, and the details that make an exceptional yacht vacation feel effortless.

Charter experts since 1987, trusted by more than 10,000 happy clients worldwide. Let us help you plan your next extraordinary escape.

#stbarth #stbarts #luxurytravel #luxuryislands #nyestbarth by @vi_sailing

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5 days ago

HAVE A SPOOKTACULAR OCTOBER! 👻
Wishing you smooth sailing and plenty of adventures for the rest of 2026.
Virgin Island Sailing®. Charter Experts since 1987 ⛵️ taken in Jost Van Dyke, British Virgin Islands by @vi_sailing

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18 days ago

This is what the Virgin Islands looks like while you’re freezing this winter

#beachtherapy #catamaransailing #vacationofalifetime #virginislandsailing #bvisailing taken in Jost Van Dyke, British Virgin Islands by @vi_sailing

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a month ago

★★★★★ Full Review 👇
“Andrew with Virgin Island Sailing was able to get us the perfect charter for a birthday celebration. INSIEME & her crew of Pete, Evan, Cindy & Jason were the best. I highly recommend this charter & the charter company.”

Meet INSIEME, a 105-foot Azimut motor yacht welcoming up to 8 guests in 5 staterooms, with a professional crew of 4 and a comfortable cruising speed of 10 knots.

Her accommodations include a King Master Stateroom, Queen VIP Stateroom, two Twin Guest Staterooms, one of which converts to a Queen, and an additional Queen Guest Stateroom.

For days on the water, INSIEME comes equipped with a 33-foot Boston Whaler tender outfitted for fishing, Sea-Doos, SeaBobs, underwater scooters, paddleboards, adult and junior wakeboards, a towable tube, floating island, snorkeling sets, fishing equipment, beach umbrellas, chairs, toys and more.

A pretty memorable way to celebrate another trip around the sun. 🥂🛥️

#luxuryvacation #stanielcay #luxurymotoryacht #virginislandsailing #luxurysuperyacht taken in Staniel Cay, Exuma Islands by @vi_sailing

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a month ago

We don’t make the social media trends. We just sail with them 😌⛵️

And apparently, some of you haven’t experienced the BVI yet… and it shows 👀 All jokes aside, consider this your sign to start planning

We’ve put together a FREE BVI Sample Itinerary to give you a taste of what your own island-hopping vacation could look like

Comment BVI and we’ll send it your way 🇻🇬

#beachtherapy #catamaransailing #vacationofalifetime #virginislandsailing #bvisailing taken in Jost Van Dyke, British Virgin Islands by @vi_sailing

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a month ago

Some of us are never ready for sweater weather☀️🌴

We’ll take Caribbean sunshine, warm water and trade winds any season of the year ⛵

#beachtherapy #catamaransailing #vacationofalifetime #virginislandsailing #bvisailing taken in Jost Van Dyke, British Virgin Islands by @vi_sailing

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2 months ago

Virgin Island Sailing® books catamaran charters worldwide, and one of our most sought-after destinations is La Bella Italia 🇮🇹⛵️

Here’s what one of our clients shared after their family vacation:

“We would absolutely recommend Virgin Island Sailing® and especially Captain Alessandro to anyone considering a sailing vacation in this region. Alessandro truly made the trip for our family, and our experience would not have been the same without him. It was an incredible week and a trip we will remember for the rest of our lives.”

Comment AMALFI to read the full review and see what it’s really like to explore Italy by yacht.

#vacationofalifetime #catamaransailing #vacationmodeon😎🌴☀️ #sailitalia #amalfivacations by @vi_sailing

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2 months ago